Sodium borohydride → HCID 178428310, compound

HRID 595292Notes

Reaction equation

HRID 595292 reaction equation
[BH4-].[Na+].[CH3:3][C:4]1[CH:5]=[C:6]([C:21]2[CH:22]=[N:23][N:24]([CH:26]3[CH2:31][CH2:30][C:29](=[O:32])[CH2:28][CH2:27]3)[CH:25]=2)[CH:7]=[C:8]([NH:10][C:11]2[N:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:14]=[CH:13][N:12]=2)[CH:9]=1>CO.CCOC(C)=O>[CH3:3][C:4]1[CH:5]=[C:6]([C:21]2[CH:22]=[N:23][N:24]([C@@H:26]3[CH2:31][CH2:30][C@H:29]([OH:32])[CH2:28][CH2:27]3)[CH:25]=2)[CH:7]=[C:8]([NH:10][C:11]2[N:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:14]=[CH:13][N:12]=2)[CH:9]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 118208899HCID 118208899, compound

Product 1

HCID 178428310HCID 178428310, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium borohydride (3.39 mg, 0.09 mmol) was added to 4-[4-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1H-pyrazol-1-yl]cyclohexanone (24.8 mg, 0.06 mmol) dissolved in methanol (0.5 mL). The reaction mixture was stirred at room temperature for one hour. The mixture was diluted with EtOAc, washed with water, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by reverse phase HPLC (45 to 80% ACN/Water with 0.1% TFA modifier). The free base was liberated using PL-HCO3 cartridges (Stratospheres™, 0.9 mmol) and lyophilized to afford cis-4-[4-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1H-pyrazol-1-yl]cyclohexanol. MS ESI calcd. for C21H23F3N5O [M+F]+ 418. found 418. 1H NMR (500 MHz, DMSO-d6) δ 10.10 (s, 1H), 8.80 (d, J=4.7 Hz, 1H), 8.06 (s, 1H), 7.82 (s, 1H), 7.70 (s, 1H), 7.38 (s, 1H), 7.25 (d, J=4.7 Hz, 1H), 7.05 (s, 1H), 4.67 (s, 1H), 4.19-4.07 (m, 1H), 3.50-3.41 (m, 1H), 2.27 (s, 3H), 2.02-1.99 (m, 2H), 1.94-1.85 (m, 2H), 1.78 (q, J=11.7 Hz, 2H), 1.35 (q, J=11.7 Hz, 2H).

Workup

  1. washwashed with water
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by reverse phase HPLC (45 to 80% ACN/Water with 0.1% TFA modifier)

Sources & evidence

ORD record
ord-b616ea96def54bf8a15c9ccf4888be20
Source dataset
uspto-grants-2016_01
Patent number
US09242984B2

Reaction notes

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